反応 #1885044

反応方程式

(R)-2-(tert-butyldiphenylsilyloxy)-4-hydroxy-N-phenylbutanamide

tert-butyl-N-tert-butoxycarbonyliminocarbamate

→

(R)-3-(tert-butyldiphenylsilyloxy)-1-phenylpyrrolidin-2-one

収率 99.9%

溶媒

THF

THF

反応条件

後処理

1. 1
   その他the cooling bath was removed
2. 2
   温度The reaction mixture was then cooled to 0° C.
3. 3
   その他the cooling bath removed
4. 4
   workup.STIRRINGthe reaction mixture stirred at RT for 45 min
5. 5
   workup.ADDITIONThe reaction mixture was poured into water
6. 6
   抽出extracted with EtOAc (3×)
7. 7
   洗浄The combined organics were washed with water (2×), brine
8. 8
   乾燥dried over MgSO4
9. 9
   その他evaporated to dryness
10. 10
    その他Purification by silica gel chromatography (1-10% EtOAc in hexane)

実験手順

To a solution of tert-butyl-N-tert-butoxycarbonyliminocarbamate (2.44 g, 10.61 mmol) in THF (17.25 mL) at 0° C. was added n-tributylphosphine (2.15 g, 2.64 mL, 10.61 mmol) dropwise, the cooling bath was removed and the reaction mixture stirred at RT for 20 min. The reaction mixture was then cooled to 0° C. and a solution of (R)-2-(tert-butyldiphenylsilyloxy)-4-hydroxy-N-phenylbutanamide (1.15 g, 2.65 mmol) in THF (17.25 mL) was added slowly, the cooling bath removed and the reaction mixture stirred at RT for 45 min. The reaction mixture was poured into water and extracted with EtOAc (3×). The combined organics were washed with water (2×), brine, dried over MgSO4 and evaporated to dryness. Purification by silica gel chromatography (1-10% EtOAc in hexane) afforded (R)-3-(tert-butyldiphenylsilyloxy)-1-phenylpyrrolidin-2-one (1.1 g, 96%) as an oil. 1H-NMR (400 MHz, DMSO-d6) δ 7.81 (dd, J=1.5, 7.7 Hz, 2H), 7.72-7.66 (m, 4H), 7.51-7.36 (m, 8H), 7.15 (m, 1H), 4.51 (dd, J=8.1, 9.2 Hz, 1H), 3.72-3.59 (m, 2H), 2.26-2.21 (m, 1H), 2.03-1.98 (m, 1H) and 1.06 (s, 9H) ppm. LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=416.7; tR=2.40 min.

出典